# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 182/1237 data_1 _audit_creation_method SHELXL-97 _chemical_formula_sum 'C32 H48 Li N2 O3 S2 V' _chemical_formula_weight 630.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Li' 'Li' -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'V' 'V' 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.297(5) _cell_length_b 18.880(4) _cell_length_c 17.444(3) _cell_angle_alpha 90.00 _cell_angle_beta 126.75(3) _cell_angle_gamma 90.00 _cell_volume 7203(2) _cell_formula_units_Z 8 _cell_measurement_temperature 299(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 15 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.163 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2688 _exptl_absorpt_coefficient_mu 0.422 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 299(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Kuma KM4 automatic diffractometer' _diffrn_measurement_method 'profile data from omega-2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 15 _diffrn_reflns_number 4086 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.04 _reflns_number_total 4028 _reflns_number_gt 3463 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma KM4 software 1996' _computing_cell_refinement 'Kuma KM4 software 1996' _computing_data_reduction 'Kuma KM4 software 1996' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII, 1976' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0568P)^2^+6.9353P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4028 _refine_ls_number_parameters 380 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.1064 _refine_ls_wR_factor_gt 0.1007 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.764 _refine_ls_shift/su_mean 0.013 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group V V 0.59501(2) 0.85132(2) 0.58443(3) 0.04402(16) Uani 1 d . . . Li Li 0.6840(2) 0.7524(3) 0.6189(4) 0.0555(13) Uani 1 d . . . S1 S 0.60826(4) 0.94933(5) 0.67280(7) 0.0717(3) Uani 1 d . . . S2 S 0.53071(5) 0.85941(5) 0.42125(6) 0.0769(3) Uani 1 d . . . O1 O 0.51059(9) 0.84462(10) 0.56852(16) 0.0581(6) Uani 1 d . . . O11 O 0.61493(8) 0.75439(9) 0.62411(13) 0.0427(5) Uani 1 d . . . O21 O 0.67796(8) 0.85285(9) 0.61703(13) 0.0444(5) Uani 1 d . . . N1 N 0.67968(16) 0.73021(16) 0.5011(3) 0.0744(9) Uani 1 d . . . N2 N 0.74656(16) 0.68279(18) 0.7165(2) 0.0861(10) Uani 1 d . . . C1 C 0.48962(17) 0.91091(18) 0.5807(3) 0.0718(10) Uani 1 d . . . H1A H 0.4559 0.9025 0.5842 0.086 Uiso 1 calc R . . H1B H 0.4754 0.9418 0.5266 0.086 Uiso 1 calc R . . C2 C 0.54083(17) 0.9445(2) 0.6697(3) 0.0776(11) Uani 1 d . . . H2A H 0.5501 0.9174 0.7242 0.093 Uiso 1 calc R . . H2B H 0.5291 0.9919 0.6744 0.093 Uiso 1 calc R . . C3 C 0.46454(16) 0.81023(19) 0.4810(3) 0.0774(12) Uani 1 d . . . H3A H 0.4260 0.8118 0.4725 0.093 Uiso 1 calc R . . H3B H 0.4756 0.7609 0.4844 0.093 Uiso 1 calc R . . C4 C 0.45670(16) 0.8444(2) 0.3970(3) 0.0833(12) Uani 1 d . . . H4A H 0.4355 0.8892 0.3832 0.100 Uiso 1 calc R . . H4B H 0.4320 0.8141 0.3413 0.100 Uiso 1 calc R . . C11 C 0.58510(13) 0.70254(14) 0.6355(2) 0.0450(7) Uani 1 d . . . C12 C 0.58715(14) 0.70282(16) 0.7177(2) 0.0539(8) Uani 1 d . . . C13 C 0.55677(18) 0.6490(2) 0.7275(3) 0.0746(10) Uani 1 d . . . H13 H 0.5575 0.6481 0.7815 0.089 Uiso 1 calc R . . C14 C 0.5256(2) 0.5970(2) 0.6596(4) 0.0868(13) Uani 1 d . . . H14 H 0.5052 0.5617 0.6675 0.104 Uiso 1 calc R . . C15 C 0.52461(18) 0.59744(18) 0.5811(3) 0.0742(11) Uani 1 d . . . H15 H 0.5033 0.5620 0.5355 0.089 Uiso 1 calc R . . C16 C 0.55439(14) 0.64914(15) 0.5667(2) 0.0532(8) Uani 1 d . . . C120 C 0.62419(17) 0.75677(19) 0.7950(2) 0.0661(9) Uani 1 d . . . H120 H 0.6252 0.7995 0.7641 0.079 Uiso 1 calc R . . C121 C 0.5981(2) 0.7784(3) 0.8477(3) 0.1130(17) Uani 1 d . . . H12A H 0.5991 0.7387 0.8829 0.136 Uiso 1 calc R . . H12B H 0.5567 0.7940 0.8024 0.136 Uiso 1 calc R . . H12C H 0.6222 0.8163 0.8912 0.136 Uiso 1 calc R . . C122 C 0.6895(2) 0.7318(3) 0.8647(3) 0.1119(17) Uani 1 d . . . H12D H 0.7134 0.7684 0.9107 0.134 Uiso 1 calc R . . H12E H 0.7060 0.7211 0.8305 0.134 Uiso 1 calc R . . H12F H 0.6905 0.6901 0.8970 0.134 Uiso 1 calc R . . C160 C 0.55555(16) 0.64485(17) 0.4817(2) 0.0626(9) Uani 1 d . . . H160 H 0.5712 0.6901 0.4771 0.075 Uiso 1 calc R . . C161 C 0.4929(2) 0.6334(2) 0.3877(3) 0.0986(14) Uani 1 d . . . H16A H 0.4965 0.6325 0.3362 0.118 Uiso 1 calc R . . H16B H 0.4661 0.6712 0.3776 0.118 Uiso 1 calc R . . H16C H 0.4764 0.5891 0.3898 0.118 Uiso 1 calc R . . C162 C 0.59901(18) 0.5871(2) 0.4959(3) 0.0838(12) Uani 1 d . . . H16D H 0.6012 0.5873 0.4430 0.101 Uiso 1 calc R . . H16E H 0.5844 0.5419 0.4995 0.101 Uiso 1 calc R . . H16F H 0.6389 0.5957 0.5542 0.101 Uiso 1 calc R . . C21 C 0.72306(13) 0.89768(14) 0.6400(2) 0.0462(7) Uani 1 d . . . C22 C 0.77275(14) 0.90773(16) 0.7372(2) 0.0540(8) Uani 1 d . . . C23 C 0.82013(16) 0.9525(2) 0.7586(3) 0.0763(11) Uani 1 d . . . H23 H 0.8528 0.9600 0.8223 0.092 Uiso 1 calc R . . C24 C 0.8200(2) 0.9855(2) 0.6889(4) 0.0950(14) Uani 1 d . . . H24 H 0.8521 1.0152 0.7052 0.114 Uiso 1 calc R . . C25 C 0.77211(18) 0.9746(2) 0.5947(3) 0.0799(11) Uani 1 d . . . H25 H 0.7726 0.9967 0.5474 0.096 Uiso 1 calc R . . C26 C 0.72315(15) 0.93166(16) 0.5681(2) 0.0565(8) Uani 1 d . . . C220 C 0.77581(15) 0.87058(18) 0.8162(2) 0.0621(9) Uani 1 d . . . H220 H 0.7396 0.8402 0.7865 0.074 Uiso 1 calc R . . C221 C 0.7744(2) 0.9228(3) 0.8821(3) 0.1043(15) Uani 1 d . . . H22A H 0.7731 0.8970 0.9282 0.125 Uiso 1 calc R . . H22B H 0.7389 0.9524 0.8448 0.125 Uiso 1 calc R . . H22C H 0.8105 0.9517 0.9147 0.125 Uiso 1 calc R . . C222 C 0.83211(18) 0.8233(2) 0.8752(3) 0.0889(13) Uani 1 d . . . H22D H 0.8304 0.7971 0.9208 0.107 Uiso 1 calc R . . H22E H 0.8683 0.8520 0.9085 0.107 Uiso 1 calc R . . H22F H 0.8330 0.7909 0.8337 0.107 Uiso 1 calc R . . C260 C 0.66954(16) 0.92262(17) 0.4637(2) 0.0614(9) Uani 1 d . . . H260 H 0.6452 0.8825 0.4594 0.074 Uiso 1 calc R . . C261 C 0.6888(2) 0.9063(2) 0.3998(3) 0.0917(13) Uani 1 d . . . H26A H 0.6532 0.8977 0.3357 0.110 Uiso 1 calc R . . H26B H 0.7144 0.8650 0.4234 0.110 Uiso 1 calc R . . H26C H 0.7110 0.9458 0.4001 0.110 Uiso 1 calc R . . C262 C 0.6290(2) 0.9882(2) 0.4286(3) 0.0938(13) Uani 1 d . . . H26D H 0.5938 0.9811 0.3637 0.113 Uiso 1 calc R . . H26E H 0.6516 1.0285 0.4317 0.113 Uiso 1 calc R . . H26F H 0.6161 0.9964 0.4683 0.113 Uiso 1 calc R . . C1N C 0.66865(17) 0.72009(18) 0.4296(3) 0.0648(9) Uani 1 d . . . C2N C 0.6552(2) 0.7065(3) 0.3369(3) 0.1047(15) Uani 1 d . . . H2N1 H 0.6121 0.7113 0.2878 0.126 Uiso 1 calc R . . H2N2 H 0.6678 0.6592 0.3357 0.126 Uiso 1 calc R . . H2N3 H 0.6769 0.7398 0.3257 0.126 Uiso 1 calc R . . C3N C 0.77085(16) 0.63975(18) 0.7693(3) 0.0668(10) Uani 1 d . . . C4N C 0.8023(2) 0.5857(2) 0.8401(4) 0.1145(18) Uani 1 d . . . H4N1 H 0.8413 0.6033 0.8931 0.137 Uiso 1 calc R . . H4N2 H 0.8082 0.5453 0.8130 0.137 Uiso 1 calc R . . H4N3 H 0.7785 0.5721 0.8617 0.137 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 V 0.0433(3) 0.0375(2) 0.0446(3) 0.0015(2) 0.0227(2) 0.0022(2) Li 0.064(3) 0.052(3) 0.062(3) 0.009(2) 0.044(3) 0.011(2) O21 0.0450(11) 0.0432(10) 0.0449(11) 0.0005(8) 0.0269(9) -0.0013(9) N1 0.101(3) 0.071(2) 0.078(2) 0.0015(16) 0.068(2) 0.0086(16) N2 0.096(3) 0.080(2) 0.086(2) 0.0212(19) 0.056(2) 0.0321(19) C1 0.068(2) 0.062(2) 0.097(3) 0.0024(19) 0.056(2) 0.0147(18) C2 0.087(3) 0.068(2) 0.095(3) -0.011(2) 0.064(2) 0.008(2) C3 0.052(2) 0.062(2) 0.090(3) -0.005(2) 0.027(2) -0.0010(17) C4 0.054(2) 0.084(3) 0.066(2) -0.002(2) 0.0110(18) 0.0052(19) C11 0.0438(16) 0.0380(14) 0.0550(19) 0.0093(12) 0.0304(14) 0.0069(12) C12 0.056(2) 0.0531(18) 0.060(2) 0.0089(15) 0.0387(16) 0.0071(14) C13 0.089(3) 0.074(2) 0.093(3) 0.010(2) 0.071(2) 0.001(2) C14 0.103(3) 0.063(2) 0.135(4) -0.002(2) 0.092(3) -0.015(2) C15 0.081(3) 0.052(2) 0.103(3) -0.0118(19) 0.062(2) -0.0119(18) C16 0.0552(18) 0.0388(15) 0.068(2) -0.0014(14) 0.0381(16) 0.0007(14) C120 0.079(2) 0.079(2) 0.053(2) 0.0030(17) 0.0454(19) -0.0026(19) C121 0.139(5) 0.126(4) 0.108(4) -0.032(3) 0.092(4) -0.016(3) C122 0.087(3) 0.155(5) 0.067(3) -0.008(3) 0.032(2) -0.003(3) C160 0.074(2) 0.0487(17) 0.066(2) -0.0129(15) 0.0422(18) -0.0078(16) C161 0.091(3) 0.107(3) 0.073(3) -0.020(2) 0.035(2) -0.001(2) C162 0.095(3) 0.073(2) 0.100(3) -0.012(2) 0.067(3) 0.002(2) C21 0.0469(17) 0.0399(15) 0.0556(18) -0.0017(13) 0.0327(14) 0.0028(12) C22 0.0497(18) 0.0535(18) 0.057(2) -0.0055(14) 0.0307(15) 0.0000(14) C23 0.056(2) 0.076(2) 0.080(3) -0.012(2) 0.032(2) -0.0133(18) C24 0.076(3) 0.082(3) 0.127(4) 0.001(3) 0.060(3) -0.025(2) C25 0.082(3) 0.071(2) 0.100(3) 0.018(2) 0.062(3) -0.004(2) C26 0.066(2) 0.0483(17) 0.067(2) 0.0102(15) 0.0454(18) 0.0038(15) C220 0.056(2) 0.073(2) 0.0499(19) -0.0095(15) 0.0278(16) -0.0034(16) C221 0.112(4) 0.122(4) 0.080(3) -0.019(3) 0.058(3) 0.013(3) C222 0.084(3) 0.106(3) 0.067(3) 0.010(2) 0.040(2) 0.020(2) C260 0.079(2) 0.0578(19) 0.062(2) 0.0166(15) 0.0494(19) 0.0119(16) C261 0.130(4) 0.088(3) 0.095(3) 0.010(2) 0.088(3) 0.008(3) C262 0.107(3) 0.080(3) 0.081(3) 0.022(2) 0.049(2) 0.034(2) C1N 0.071(2) 0.063(2) 0.070(3) 0.0029(18) 0.048(2) 0.0096(17) C2N 0.127(4) 0.118(4) 0.066(3) -0.005(2) 0.055(3) 0.007(3) C3N 0.064(2) 0.054(2) 0.082(3) 0.0066(18) 0.0432(19) 0.0098(17) C4N 0.096(3) 0.077(3) 0.140(4) 0.046(3) 0.055(3) 0.015(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag V O11 1.917(2) . ? V O21 1.977(2) . ? V O1 2.154(2) . ? V S2 2.286(2) . ? V S1 2.294(1) . ? V Li 2.830(5) . ? Li O21 1.903(5) . ? Li O11 1.942(6) . ? Li N2 2.015(6) . ? Li N1 2.030(6) . ? S1 C2 1.811(4) . ? S2 C4 1.821(4) . ? O1 C3 1.427(4) . ? O1 C1 1.444(4) . ? O11 C11 1.362(3) . ? O21 C21 1.342(3) . ? N1 C1N 1.110(4) . ? N2 C3N 1.103(4) . ? C1 C2 1.473(5) . ? C3 C4 1.495(6) . ? C11 C16 1.398(4) . ? C11 C12 1.402(4) . ? C12 C13 1.385(5) . ? C12 C120 1.499(5) . ? C13 C14 1.373(5) . ? C14 C15 1.355(5) . ? C15 C16 1.386(5) . ? C16 C160 1.505(5) . ? C120 C122 1.511(5) . ? C120 C121 1.516(5) . ? C160 C162 1.518(5) . ? C160 C161 1.518(5) . ? C21 C26 1.410(4) . ? C21 C22 1.413(4) . ? C22 C23 1.396(5) . ? C22 C220 1.503(5) . ? C23 C24 1.364(6) . ? C24 C25 1.372(6) . ? C25 C26 1.385(5) . ? C26 C260 1.516(5) . ? C220 C222 1.525(5) . ? C220 C221 1.533(5) . ? C260 C261 1.522(5) . ? C260 C262 1.523(5) . ? C1N C2N 1.452(6) . ? C3N C4N 1.426(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O11 V O21 83.19(8) . . ? O11 V O1 92.34(8) . . ? O21 V O1 172.20(8) . . ? O11 V S2 110.73(6) . . ? O21 V S2 104.55(7) . . ? O1 V S2 83.00(8) . . ? O11 V S1 129.11(7) . . ? O21 V S1 95.85(6) . . ? O1 V S1 81.97(7) . . ? S2 V S1 118.52(4) . . ? O11 V Li 43.19(12) . . ? O21 V Li 42.16(12) . . ? O1 V Li 134.84(12) . . ? S2 V Li 103.33(12) . . ? S1 V Li 128.29(12) . . ? O21 Li O11 84.5(2) . . ? O21 Li N2 133.3(3) . . ? O11 Li N2 109.2(3) . . ? O21 Li N1 103.7(3) . . ? O11 Li N1 125.6(3) . . ? N2 Li N1 103.2(3) . . ? O21 Li V 44.22(12) . . ? O11 Li V 42.49(11) . . ? N2 Li V 142.7(3) . . ? N1 Li V 113.5(2) . . ? C2 S1 V 100.99(12) . . ? C4 S2 V 101.39(14) . . ? C3 O1 C1 112.3(3) . . ? C3 O1 V 110.8(2) . . ? C1 O1 V 114.71(19) . . ? C11 O11 V 132.37(17) . . ? C11 O11 Li 132.4(2) . . ? V O11 Li 94.33(17) . . ? C21 O21 Li 124.7(2) . . ? C21 O21 V 141.51(17) . . ? Li O21 V 93.62(19) . . ? C1N N1 Li 170.0(4) . . ? C3N N2 Li 165.3(4) . . ? O1 C1 C2 108.6(3) . . ? C1 C2 S1 111.1(3) . . ? O1 C3 C4 111.7(3) . . ? C3 C4 S2 110.6(2) . . ? O11 C11 C16 119.8(3) . . ? O11 C11 C12 119.0(3) . . ? C16 C11 C12 121.1(3) . . ? C13 C12 C11 117.6(3) . . ? C13 C12 C120 121.2(3) . . ? C11 C12 C120 121.0(3) . . ? C14 C13 C12 121.8(4) . . ? C15 C14 C13 119.6(4) . . ? C14 C15 C16 121.9(4) . . ? C15 C16 C11 117.9(3) . . ? C15 C16 C160 120.1(3) . . ? C11 C16 C160 122.0(3) . . ? C12 C120 C122 110.3(3) . . ? C12 C120 C121 114.8(3) . . ? C122 C120 C121 110.6(4) . . ? C16 C160 C162 110.7(3) . . ? C16 C160 C161 113.4(3) . . ? C162 C160 C161 109.8(3) . . ? O21 C21 C26 120.7(3) . . ? O21 C21 C22 119.6(3) . . ? C26 C21 C22 119.6(3) . . ? C23 C22 C21 118.2(3) . . ? C23 C22 C220 120.2(3) . . ? C21 C22 C220 121.6(3) . . ? C24 C23 C22 122.0(4) . . ? C23 C24 C25 119.5(4) . . ? C24 C25 C26 121.7(4) . . ? C25 C26 C21 119.0(3) . . ? C25 C26 C260 120.8(3) . . ? C21 C26 C260 120.2(3) . . ? C22 C220 C222 111.9(3) . . ? C22 C220 C221 112.0(3) . . ? C222 C220 C221 109.7(3) . . ? C26 C260 C261 113.2(3) . . ? C26 C260 C262 109.8(3) . . ? C261 C260 C262 110.9(3) . . ? N1 C1N C2N 179.1(4) . . ? N2 C3N C4N 177.9(5) . . ? _diffrn_measured_fraction_theta_max 0.305 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.305 _refine_diff_density_max 0.395 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.039 data_2 _audit_creation_method SHELXL-97 _chemical_formula_sum 'C21 H30 N O2 S2 V' _chemical_formula_weight 443.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'V' 'V' 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.022(3) _cell_length_b 12.156(4) _cell_length_c 18.628(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.44(3) _cell_angle_gamma 90.00 _cell_volume 2244.8(11) _cell_formula_units_Z 4 _cell_measurement_temperature 299(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.5 _cell_measurement_theta_max 14 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.643 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Kuma KM4 automatic diffractometer' _diffrn_measurement_method 'profile data from omega-2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1 _diffrn_reflns_number 3526 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3384 _reflns_number_gt 3108 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma KM4 software 1996' _computing_cell_refinement 'Kuma KM4 software 1996' _computing_data_reduction 'Kuma KM4 software 1996' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII, 1976' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+0.6486P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3384 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0785 _refine_ls_wR_factor_gt 0.0760 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0.134 _refine_ls_shift/su_mean 0.008 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group V V 0.04740(3) 0.20720(3) 0.891791(17) 0.03007(10) Uani 1 d . . . S1 S -0.13949(5) 0.11801(5) 0.83316(3) 0.04578(15) Uani 1 d . . . S2 S 0.13326(5) 0.17077(5) 1.01071(3) 0.04262(14) Uani 1 d . . . O1 O 0.15039(13) 0.06109(11) 0.87076(7) 0.0372(3) Uani 1 d . . . O2 O 0.14415(12) 0.29697(11) 0.83692(7) 0.0333(3) Uani 1 d . . . N N -0.06687(15) 0.34556(13) 0.91786(9) 0.0353(4) Uani 1 d . . . C1 C 0.0873(2) 0.00804(18) 0.80480(12) 0.0458(5) Uani 1 d . . . C2 C -0.0617(2) -0.00881(19) 0.80592(13) 0.0516(6) Uani 1 d . . . C3 C 0.1716(2) -0.01345(17) 0.93236(12) 0.0463(5) Uani 1 d . . . C4 C 0.2338(2) 0.04985(19) 0.99724(12) 0.0486(5) Uani 1 d . . . C11 C -0.0969(2) 0.42680(19) 0.86994(12) 0.0490(5) Uani 1 d . . . C12 C -0.1674(2) 0.51935(19) 0.88430(14) 0.0554(6) Uani 1 d . . . C13 C -0.2080(2) 0.52956(19) 0.95154(14) 0.0512(6) Uani 1 d . . . C14 C -0.1794(2) 0.4471(2) 1.00059(13) 0.0516(6) Uani 1 d . . . C15 C -0.1103(2) 0.35607(18) 0.98196(12) 0.0446(5) Uani 1 d . . . C21 C 0.22727(18) 0.26724(14) 0.78875(10) 0.0307(4) Uani 1 d . . . C22 C 0.36504(19) 0.24917(16) 0.81320(10) 0.0337(4) Uani 1 d . . . C23 C 0.4461(2) 0.21620(18) 0.76231(12) 0.0443(5) Uani 1 d . . . C24 C 0.3934(2) 0.20285(19) 0.69015(12) 0.0512(6) Uani 1 d . . . C25 C 0.2594(2) 0.22443(17) 0.66711(11) 0.0452(5) Uani 1 d . . . C26 C 0.1738(2) 0.25765(16) 0.71515(10) 0.0356(4) Uani 1 d . . . C220 C 0.4217(2) 0.27074(18) 0.89149(11) 0.0406(5) Uani 1 d . . . C221 C 0.5501(3) 0.2083(3) 0.91810(15) 0.0728(8) Uani 1 d . . . C222 C 0.4427(3) 0.3941(2) 0.90285(15) 0.0651(7) Uani 1 d . . . C260 C 0.0280(2) 0.28772(18) 0.69004(12) 0.0447(5) Uani 1 d . . . C261 C 0.0146(3) 0.4103(2) 0.67558(18) 0.0711(8) Uani 1 d . . . C262 C -0.0390(3) 0.2214(3) 0.62572(18) 0.0837(10) Uani 1 d . . . H1A H 0.1301 -0.0626 0.7997 0.055 Uiso 1 calc R . . H1B H 0.1000 0.0530 0.7633 0.055 Uiso 1 calc R . . H2A H -0.0746 -0.0673 0.8397 0.062 Uiso 1 calc R . . H2B H -0.1050 -0.0307 0.7580 0.062 Uiso 1 calc R . . H3A H 0.2307 -0.0732 0.9227 0.056 Uiso 1 calc R . . H3B H 0.0862 -0.0446 0.9409 0.056 Uiso 1 calc R . . H4A H 0.3241 0.0725 0.9908 0.058 Uiso 1 calc R . . H4B H 0.2408 0.0032 1.0399 0.058 Uiso 1 calc R . . H11 H -0.0688 0.4205 0.8247 0.059 Uiso 1 calc R . . H12 H -0.1873 0.5739 0.8494 0.067 Uiso 1 calc R . . H13 H -0.2542 0.5919 0.9631 0.061 Uiso 1 calc R . . H14 H -0.2062 0.4520 1.0462 0.062 Uiso 1 calc R . . H15 H -0.0931 0.2993 1.0155 0.054 Uiso 1 calc R . . H23 H 0.5374 0.2030 0.7773 0.053 Uiso 1 calc R . . H24 H 0.4485 0.1793 0.6571 0.061 Uiso 1 calc R . . H25 H 0.2253 0.2166 0.6182 0.054 Uiso 1 calc R . . H220 H 0.3536 0.2474 0.9211 0.049 Uiso 1 calc R . . H22A H 0.5758 0.2213 0.9691 0.087 Uiso 1 calc R . . H22B H 0.6207 0.2330 0.8923 0.087 Uiso 1 calc R . . H22C H 0.5352 0.1311 0.9098 0.087 Uiso 1 calc R . . H22D H 0.4703 0.4087 0.9535 0.078 Uiso 1 calc R . . H22E H 0.3598 0.4320 0.8865 0.078 Uiso 1 calc R . . H22F H 0.5112 0.4191 0.8757 0.078 Uiso 1 calc R . . H260 H -0.0213 0.2719 0.7305 0.054 Uiso 1 calc R . . H26A H -0.0791 0.4302 0.6679 0.085 Uiso 1 calc R . . H26B H 0.0541 0.4283 0.6331 0.085 Uiso 1 calc R . . H26C H 0.0603 0.4500 0.7165 0.085 Uiso 1 calc R . . H26D H 0.0023 0.2388 0.5837 0.100 Uiso 1 calc R . . H26E H -0.1333 0.2392 0.6164 0.100 Uiso 1 calc R . . H26F H -0.0284 0.1444 0.6363 0.100 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 V 0.02993(17) 0.03039(18) 0.03136(17) 0.00100(12) 0.00944(12) 0.00135(13) S1 0.0353(3) 0.0474(3) 0.0551(3) -0.0043(2) 0.0079(2) -0.0035(2) S2 0.0487(3) 0.0442(3) 0.0349(3) 0.0031(2) 0.0060(2) 0.0038(2) O1 0.0405(7) 0.0314(7) 0.0419(7) 0.0024(6) 0.0138(6) 0.0033(6) O2 0.0324(7) 0.0346(7) 0.0351(7) 0.0014(5) 0.0116(5) -0.0001(5) N 0.0321(8) 0.0357(9) 0.0394(9) -0.0005(7) 0.0090(7) 0.0029(7) C1 0.0576(13) 0.0361(11) 0.0466(12) -0.0061(9) 0.0169(10) 0.0012(10) C2 0.0593(14) 0.0423(12) 0.0532(13) -0.0096(10) 0.0083(11) -0.0066(11) C3 0.0537(13) 0.0347(11) 0.0533(13) 0.0108(9) 0.0167(10) 0.0094(9) C4 0.0464(12) 0.0471(13) 0.0517(13) 0.0124(10) 0.0052(10) 0.0088(10) C11 0.0513(12) 0.0511(13) 0.0472(12) 0.0076(10) 0.0157(10) 0.0114(10) C12 0.0546(13) 0.0438(13) 0.0694(16) 0.0136(12) 0.0145(12) 0.0136(11) C13 0.0425(12) 0.0407(12) 0.0717(15) -0.0102(11) 0.0127(11) 0.0090(10) C14 0.0529(13) 0.0546(14) 0.0505(13) -0.0049(11) 0.0184(10) 0.0126(11) C15 0.0482(12) 0.0452(12) 0.0430(11) 0.0034(9) 0.0156(9) 0.0096(9) C21 0.0344(9) 0.0252(9) 0.0345(10) 0.0014(7) 0.0119(8) -0.0025(7) C22 0.0353(10) 0.0297(9) 0.0375(10) -0.0004(8) 0.0102(8) -0.0014(8) C23 0.0391(11) 0.0459(12) 0.0505(13) -0.0010(10) 0.0156(9) 0.0062(9) C24 0.0617(14) 0.0523(14) 0.0446(12) -0.0069(10) 0.0242(11) 0.0087(11) C25 0.0614(14) 0.0406(12) 0.0347(11) -0.0039(9) 0.0109(10) -0.0015(10) C26 0.0431(11) 0.0284(9) 0.0358(10) 0.0042(8) 0.0078(8) -0.0038(8) C220 0.0320(10) 0.0503(12) 0.0403(11) -0.0022(9) 0.0078(8) -0.0005(9) C221 0.0559(15) 0.101(2) 0.0567(16) -0.0126(15) -0.0087(12) 0.0250(15) C222 0.0761(17) 0.0603(16) 0.0585(15) -0.0218(13) 0.0080(13) -0.0111(13) C260 0.0429(11) 0.0514(13) 0.0387(11) 0.0083(9) 0.0019(9) -0.0045(9) C261 0.0567(15) 0.0593(16) 0.098(2) 0.0231(15) 0.0142(14) 0.0137(13) C262 0.0715(19) 0.091(2) 0.078(2) -0.0133(17) -0.0251(16) -0.0004(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag V O2 1.8619(13) . ? V O1 2.1195(14) . ? V N 2.1306(17) . ? V S1 2.2970(9) . ? V S2 2.2987(8) . ? S1 C2 1.833(2) . ? S2 C4 1.820(2) . ? O1 C1 1.448(3) . ? O1 C3 1.453(2) . ? O2 C21 1.360(2) . ? N C11 1.336(3) . ? N C15 1.335(3) . ? C1 C2 1.510(3) . ? C3 C4 1.490(3) . ? C11 C12 1.376(3) . ? C12 C13 1.378(3) . ? C13 C14 1.359(3) . ? C14 C15 1.376(3) . ? C21 C26 1.402(3) . ? C21 C22 1.406(3) . ? C22 C23 1.395(3) . ? C22 C220 1.508(3) . ? C23 C24 1.380(3) . ? C24 C25 1.374(3) . ? C25 C26 1.387(3) . ? C26 C260 1.512(3) . ? C220 C221 1.514(3) . ? C220 C222 1.524(3) . ? C260 C262 1.516(3) . ? C260 C261 1.516(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 V O1 94.74(6) . . ? O2 V N 90.18(6) . . ? O1 V N 175.07(6) . . ? O2 V S1 118.01(5) . . ? O1 V S1 84.37(5) . . ? N V S1 93.04(5) . . ? O2 V S2 119.37(5) . . ? O1 V S2 83.86(4) . . ? N V S2 94.02(5) . . ? S1 V S2 122.08(3) . . ? C2 S1 V 100.27(8) . . ? C4 S2 V 99.16(8) . . ? C1 O1 C3 112.80(16) . . ? C1 O1 V 111.48(12) . . ? C3 O1 V 113.29(11) . . ? C21 O2 V 128.71(12) . . ? C11 N C15 117.12(18) . . ? C11 N V 120.47(14) . . ? C15 N V 122.40(14) . . ? O1 C1 C2 110.97(17) . . ? C1 C2 S1 110.58(15) . . ? O1 C3 C4 108.29(17) . . ? C3 C4 S2 110.76(15) . . ? N C11 C12 123.1(2) . . ? C11 C12 C13 118.6(2) . . ? C14 C13 C12 118.9(2) . . ? C13 C14 C15 119.2(2) . . ? N C15 C14 123.0(2) . . ? O2 C21 C26 118.97(16) . . ? O2 C21 C22 119.69(17) . . ? C26 C21 C22 121.32(17) . . ? C23 C22 C21 117.84(18) . . ? C23 C22 C220 122.21(18) . . ? C21 C22 C220 119.88(17) . . ? C24 C23 C22 121.2(2) . . ? C25 C24 C23 119.94(19) . . ? C24 C25 C26 121.5(2) . . ? C25 C26 C21 118.14(18) . . ? C25 C26 C260 122.11(19) . . ? C21 C26 C260 119.71(17) . . ? C22 C220 C221 114.25(18) . . ? C22 C220 C222 109.27(18) . . ? C221 C220 C222 110.7(2) . . ? C26 C260 C262 114.3(2) . . ? C26 C260 C261 110.43(19) . . ? C262 C260 C261 111.4(2) . . ? _diffrn_measured_fraction_theta_max 0.809 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.809 _refine_diff_density_max 0.212 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.058